1785-86 James Mitchell, Head Master
1788-89 Elias Jones, Head Master
1789-91 Isaac Wilson, Head Master
1791-93 James Moore, Head Master
1793-94 James Moore, Acting President
1794-96 Harry Toulmin, First Official President
1796-99 James Moore, President
1799-1804 James Moore, President
1804-1818 James Blythe, Acting President
1818-1827 Horace Holley, President
Article on Holley from Kentucky Encyclopedia
1828-1831 Alva Woods, President
1831-1833 John [Mansfield] Lutz, Acting President
1833-1834 Benjamin Orr Peers, Acting President
1834-1835 John [Mansfield] Lutz, Acting President
1835-1837 Thomas Coit, President
1838-1839 Louis Marshall, President
1840-1842 Robert Davidson, President
1842-1849 Henry B. Bascom, President
1849-1856 James B. Dodd, President
1856-1858 Lewis Warner Green, President
Transylvania Preparatory School (High School) 1858 – 1865
1858-1861 Abraham Drake, Principal
1861-1865 James Kennedy Patterson, Principal
Kentucky University at Harrodsburg 1859-1864
1859-1865 Robert Milligan, President
1865-1878 John Bryan Bowman, Regent
Article from Kentucky Encyclopedia
1878-1880 Henry Hall White, President
1880-1897 Charles Louis Loos, President
1897-1900 Reuben L. Cave, President
1900-1901 Alexander Reed Milligan, Acting President
1901-1906 Burris A. Jenkins, President
1906-1908 Thomas Benton McCartney, Acting President
1908-1921 Richard Henry Crossfield, President
1921-1922 Thomas Benton McCartney, Acting President
1922-1928 Andrew Davidson Harmon, President
1928-1929 Thomas Benton McCartney, Acting President
1929-1930 Elmer Grant Campbell, Acting President
1930-1938 Arthur Braden, President
1938-1939 Richard Henry Crossfield, Interim President
1939-1943 Raymond F. McLain, President
1943-1945 Leland A. Brown, Acting President
1946-1951 Raymond F. McLain, President
1951-1957 Frank A. Rose, President
1958-1976 Irvin E. Lunger, President
1976-1981 William W. Kelly, President
1981-1982 Irvin E. Lunger, Interim President
1982-1983 David G. Brown, President
1983-2010 Charles L. Shearer, President
8/1/2010-6/30/2014 R. Owen Williams, President
7/1/2014-8/2/2019 Seamus Carey, President
8/15/2019-6/30/2020 John N. Williams, Interim President
7/1/2020-present Brien Lewis, President